(2S,3R,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2S,3R,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol
CAS No.:203172-21-8
Molecular Formula:C₂₉H₃₆O₄Si
Molecular Weight:476.688
Hs Code.:

Synonyms:(2S,3R,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

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Chemical Property of (2S,3R,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

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Technology Process of (2S,3R,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

There total 8 articles about (2S,3R,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 203172-20-7
(2S,3R,6S)-2-Benzyloxy-6-hydroxymethyl-tetrahydro-pyran-3-ol

: 203172-21-8
(2S,3R,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

Guidance literature:: With 1H-imidazole;
DOI:10.1016/0040-4039(96)01265-8

Reference yield:

: 86196-36-3
benzyl α-D-galactopyranoside

: 203172-21-8
(2S,3R,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 8 steps

1: TsOH / acetone / 7 h / 0 °C

2: pyridine / 20 h / Ambient temperature

3: 80 percent / aq. AcOH / 4 h / 50 °C

4: 90 percent / acetonitrile / 5 h / Ambient temperature

5: 80 percent / trimethyl phosphite / 4.5 h / Heating

6: 85 percent / H₂ / Pd(OH)2/C / ethanol / 5 h / Ambient temperature

7: 100 percent / K₂CO₃ / methanol / 3 h / Ambient temperature

8: 79 percent / imidazole / dimethylformamide / 0.08 h / Ambient temperature

With 1H-imidazole; hydrogen; potassium carbonate; toluene-4-sulfonic acid; acetic acid; phosphorous acid trimethyl ester; palladium dihydroxide; In pyridine; methanol; ethanol; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/jo972023a

Reference yield:

: 182622-28-2
Benzyl 3,4-O-isopropylidene-α-D-galactopyranoside

: 203172-21-8
(2S,3R,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / 20 h / Ambient temperature

2: 80 percent / aq. AcOH / 4 h / 50 °C

3: 90 percent / acetonitrile / 5 h / Ambient temperature

4: 80 percent / trimethyl phosphite / 4.5 h / Heating

5: 85 percent / H₂ / Pd(OH)2/C / ethanol / 5 h / Ambient temperature

6: 100 percent / K₂CO₃ / methanol / 3 h / Ambient temperature

7: 79 percent / imidazole / dimethylformamide / 0.08 h / Ambient temperature

With 1H-imidazole; hydrogen; potassium carbonate; acetic acid; phosphorous acid trimethyl ester; palladium dihydroxide; In pyridine; methanol; ethanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo972023a